Resin acid ester and method of producing



Patented Feb. 2, 1932 IRVIN w. HUM PHR ni foF wnAnroN, NEW JERSEY, ns'srenonro nnncunns rownnn 7 COMPANY; on wrmvrme'ron, DELAWARE; CORPORATION1OE'DELAWARE H REsI'riAcrn ESTERAND Mmaeuprisspwqn- No Drawing.

My invention relates to resin acid esters and method of producing and more particularly relates to resin acid esters prepared from a dichloro ether and to the method forproducing such esters.

In carrying the method in accordance With my invention into practice for'the prepara tion of esters embodying my invention, the

resin acid to be esterified is heated With a.

chloro ether in the presence-of an alkali and desirably also, though not necessarilyin all cases, of alcohol, excess chloro ether, any excess alcohol, if, present, and free resin acid darac, pontianak, etc. Various chloro ethers may be used, as for example, dichloroethyl ether, chloromethyl ether and s-dichloro dimethyl ether, etc., for the production of various resin acid esters. In carrying out the treatment various alkalis, as for example, sodium hydroxide, sodium carbonate, lime, potassium hydroxide, and the like, may be used and such alcohols, as ethyl, amyl, "isopropyl, butyl, etc., will be found satisfactory as solvents.

By Way of illustration, the diglycol diabie-,

tate ester of'rosin may be prepared by heating rosin and diglycoltogethenor by heating to gethersodium abietate and B, B dich1oroethyl ether, preferably in alcoholic solution. Where the dichloroethyl ether is heated, preferably under pressure, With alcoholic sodium.

resinate, both chlorine atoms are removed with the formation of diglycol diabietate. *The reaction may be illustrated asfollows:

As a more specific example of the preparation of the diglycol ester of rosin, for'ex- Application filed October 9, 1929. jserfiai 358,578.,

ample, a solutionjof '60-'parts' of sodium hy droxide and 500 parts'ofrosin in'7O0 parts of alcohol are heated With-110 parts of 15, 13" di chloroethyl ether for-say about-eight hours at a temperatureof'about 160 C. and under a pressure 'of about *175 pounds. After the under atmospheric pressure and asmall amountof free rosin is removed byyheating to sayabout'3O0 C; under a pressureofab'out V one half inch of mercury. Tillie residue, about 430 g. obtained after removal of the alcohol and free rosin 'Will consist ofdiglycol diabietatefvvhich vvill be somewhat softer than rosin-and will have an acid number of 5;

As further illustration of, the-practical adaptation, of my invention, for example-,'ja

rosin estermay be produced by refluxing g, of drysodium resinate, 300 g. of henzene and25 g. of s dichloro dimethyl ether for about 'ten hours, then; Water Washing the solution .to remove-soap and distillin goif the b'enz'en'ej The -product willjamountfto about 110 ggand will have a melting point, ofabout by, for example, distillation under reduced pressure; r i i c :1 If desired: I e iesters produced in accordw vi'th "i vention may b fh d e g fluted as for i ll j gthem'to a strea nof'hydrogen in the, presence of a palladium oriplatinum catalyst at room temperature, or, for example, in the presence of a -nickel, catalyst at an'elevated temperature.

illhe hydrogenation isidesirably, tliiough not necessarily, carried out under pressure.

: {It W111 now be; 'noted that in accordance with my nvention; variousresin esters pro-.

duced from chloroethers arerendered.avail-v ahle- ,ai1clj git-Will be, understood that I doinot V intend that my invention shall be limited to the v(precise :details set .forth' hereinuiz Having nowlfullydescribed myinvention,

e1aiiimnduesireto protect by Letters Patent w 1. The method of producing ajresinester 'i' io' which includes heating a natural resin with.

an aliphatic chloro-oxy ether inthe resence of an alkali and a monohydric alcoho 5. The method of producing an abietic acid ester which includes esterifying abietic acid with an aliphatic chloro-oxy ether.

6. The method of producing an abietic acid ester which includes esteri fying aloietic acid with a chloroethylether.

7. The method of producing a rosin acid ester which includes heating rosin with an alipathic dichloro-o'xy ether in thepresence of an alkali,

8. Themethod of producing a rosin acid ester which includes heating. rosin with dichloroethyl ether'in the presence of analka li and a monohydricalcohol.

19. The method of producing a resin acid ester which includes esterifying a rosin with a chloro methyl ether in the presence of an alkali and of a monohydric alcohol.

20. The method of producing a resin acid ester which includes esterifyinga rosin with s-dichloro dimethyl ether in the presence o1 an alkali and of a monohydric alcohol.

In testimony of which invention, I have hereuntoset my hand at Kenvil, N. J on' this lth day of October, 1929.

IBYI N W. HUMPHREY.

9. The method of-producing an ester of.

abietic acid which includes heating sodium abietate with an aliphatic chloro-03y ether.

19. The method of producing anester of abietic acidwhich includes heating sodium abietate with an alipathic s dichloro oxy ether.

11. The method of producing diglycol diahietate which includes esterifying abietic acid with B, B dichlorethyl ether.

12. The methodof producing diglycoldiabietate which includes esterit'yingabietic acid with By B dichlorethyl ether in the presence of a monohydric alcohol.

13. The method of producingdiglycol diabietate which includes heatingrosin and an alkali with B, B dichlorethyl ether.

14. The method of producing diglycol diabietate which includes heating rosin and an alkali with B, B dichlor-ethyl etherin the presence of anon-reactive solvent for the rosin.

15. The method of producing a resin acid ester which includes esterifying a rosin with a chloro methyl ether.

16. The method of producing a resin acid ester which includes esterifying a rosin with s-dichloro dimethyl ether.

17. The method of producing a resin acid ester which includes esterifying a rosin with a chloro methyl ether in the presence of an alkali and of a non-reactive solvent for the rosin. V

18. The method of producingaresinacid ester which includes esterifyingarosin with s-dichloro dimethyl ether in the presence of an alkali and of a non-reactive solvent forthe lOSlIl. 1 

